Acetoacetylated polymers crosslinked with carbamylmethylaminotriazines

Abstract

This invention provides curable coating compositions which contain acetoacetylated polymers and carbamylmethylaminotriazine crosslinking agents. Active hydrogen containing materials and cure catalysts can, optionally, be added to the curable compositions made in accordance with this invention. The invention further provides articles of manufacture having at least one substrate coated with a curable composition which contains acetoacetylated polymers and triazine crosslinking agents.

That which is claimed is: 
     
       1. A curable coating composition comprising: (a) an acetoacetylated polymer, and   (b) a triazine compound selected from the group consisting of: (i) triaminotriazine compounds of the formula   C.sub.3 N.sub.6 (CH.sub.2 OR).sub.6-x (CH.sub.2 NHCOOR').sub.x,       (ii) benzoguanamine compounds of the formula   C.sub.3 N.sub.5 (C.sub.6 H.sub.5)(CH.sub.2 OR).sub.4-y (CH.sub.2 NHCOOR').sub.y,       (iii) oligomers of (i) or of (ii), and   (iv) mixtures of at least two of any of (i), (ii) and (iii), wherein the R and R' groups are, independently, radicals derived from monoalkyl ethers of alkylene glycols having at least 4 carbon atoms and monoaryl ethers of alkylene glycols having at least 8 carbon atoms, alone or combined with alkyl groups having from 1 to 20 carbon atoms, where x is in the range of from 2 to 6, and where y is in the range of from 2 to 4.       
     
     
       2. A curable coating composition as in claim 1, wherein the R and R' groups are derived from monoalkyl ethers of alkylene glycols having from 4 to 12 carbon atoms alone or combined with alkyl groups having 1 to 4 carbon atoms. 
     
     
       3. A curable coating composition as in claim 2, wherein the R and R' groups are derived from monoalkyl ethers of propylene glycol, diethylene glycol or dipropylene glycol. 
     
     
       4. A curable coating composition as in claim 1, wherein x is in the range of from 3 to 6, and wherein y is in the range of from 3 to 4. 
     
     
       5. A curable coating composition as in claim 1 further comprising an active hydrogen containing material. 
     
     
       6. A curable coating composition as in claim 5, wherein the active hydrogen containing material comprises a polymeric material having at least one active hydrogen selected from the group consisting of carboxylic acid, hydroxy, amino, amido, thiol and mixtures thereof. 
     
     
       7. A curable coating composition as in claim 5, wherein the active hydrogen containing polymeric material comprises a compound selected from the group consisting of hydroxy functional acrylic polymers, hydroxy functional polyesters, hydroxy functional polyurethanes, hydroxy functional epoxy polymers, hydroxy functional epoxy-amine reaction product polymers and mixtures thereof. 
     
     
       8. A curable coating composition as in claim 5 further comprising a cure catalyst. 
     
     
       9. A curable coating composition as in claim 8, wherein the cure catalyst comprises a compound selected from the group consisting of a tin catalyst alone and a tin catalyst in combination with an acid catalyst. 
     
     
       10. A curable coating composition as in claim 1, wherein components (a) and (b) are dispersed in water or in mixtures of water and organic solvent. 
     
     
       11. A curable coating composition as in claim 1, wherein the triazine compound is present in an amount of at least 5 percent by weight based on total weight of the curable coating composition. 
     
     
       12. A curable coating composition as in claim 1, wherein the weight ratio of the triazine compound to the acetoacetylated polymer ranges from 1:20 to 1:12. 
     
     
       13. A curable coating composition as in claim 1, wherein the acetoacetylated polymer has the general formula: ##STR6## wherein Φ is a polymeric backbone. 
     
     
       14. A curable coating composition as in claim 13, wherein the acetoacetylated polymer is selected from the group consisting of acetoacetylated polyesters and acetoacetylated acrylics. 
     
     
       15. A curable coating composition comprising: (a) an acetoacetylated polymer, and   (b) a triazine compound selected from the group consisting of: (i) triaminotriazine compounds of the formula   C.sub.3 N.sub.6 (CH.sub.2 OR).sub.6-x (CH.sub.2 NHCOOR').sub.x,       (ii) benzoguanamine compounds of the formula   C.sub.3 N.sub.5 (C.sub.6 H.sub.5)(CH.sub.2 OR).sub.4-y (CH.sub.2 NHCOOR').sub.y,       (iii) oligomers of (i) or of (ii), and     (iv) mixtures of at least two of any of (i), (ii) and (iii), wherein the R groups are, independently, hydrogen or alkyl groups of from 1 to 12 carbon atoms, where the R' groups are, independently, alkyl groups of from 1 to 20 carbon atoms, where x is in the range of from 2 to 6, and where y is in the range of from 2 to 4.     
     
     
       16. A curable coating composition as in claim 15, wherein components (a) and (b) are dispersed in water or in mixtures of water and organic solvent. 
     
     
       17. A curable coating composition as in claim 15, wherein the triazine compound is present in an amount of at least 5 percent by weight based on total weight of the curable coating composition. 
     
     
       18. A curable coating composition as in claim 15, wherein the weight ratio of the triazine compound to the acetoacetylated polymer ranges from 1:20 to 1:12. 
     
     
       19. A curable coating composition as in claim 15, wherein the acetoacetylated polymer has the general formula: ##STR7## wherein Φ is a polymeric backbone. 
     
     
       20. A curable coating composition as in claim 19, wherein the acetoacetylated polymer is selected from the group consisting of acetoacetylated polyesters and acetoacetylated acrylics. 
     
     
       21. A curable coating composition comprising: (a) an acetoacetylated polymer, and   (b) a triazine compound selected from the group consisting of: (i) triaminotriazine compounds of the formula   C.sub.3 N.sub.6 (CH.sub.2 OR).sub.6-x (CH.sub.2 NHCOOR').sub.x,       (ii) benzoguanamine compounds of the formula   C.sub.3 N.sub.5 (C.sub.6 H.sub.5)(CH.sub.2 OR).sub.4-y (CH.sub.2 NHCOOR').sub.y,       (iii) oligomers of (i) or of (ii), and   (iv) mixtures of at least two of any of (i), (ii) and (iii), wherein the R groups are, independently, hydrogen or alkyl groups of from 1 to 12 carbon atoms, where the R' groups are, independently, beta-hydroxyalkyl groups of from 2 to 18 carbon atoms, alone, or combined with alkyl groups of from 1 to 18 carbon atoms, where x is in the range of from 3 to 6, and where y is in the range of from 2 to 4.       
     
     
       22. A curable coating composition as in claim 21, wherein components (a) and (b) are dispersed in water or in mixtures of water and organic solvent. 
     
     
       23. A curable coating composition as in claim 21, wherein the triazine compound is present in an amount of at least 5 percent by weight based on total weight of the curable coating composition. 
     
     
       24. A curable coating composition as in claim 21, wherein the weight ratio of the triazine compound to the acetoacetylated polymer ranges from 1:20 to 1:12 
     
     
       25. A curable coating composition as in claim 21, wherein the acetoacetylated polymer has the general formula: ##STR8## wherein Φ is a polymeric backbone. 
     
     
       26. A curable coating composition as in claim 25, wherein the acetoacetylated polymer is selected from the group consisting of acetoacetylated polyesters and acetoacetylated acrylics. 
     
     
       27. An article of manufacture comprising at least one surface coated with a curable coating composition, wherein said composition comprises: (a) an acetoacetylated polymer, and   (b) a triazine compound selected from the group consisting of: (i) triaminotriazine compounds of the formula   C.sub.3 N.sub.6 (CH.sub.2 OR).sub.6-x (CH.sub.2 NHCOOR').sub.x,       (ii) benzoguanamine compounds of the formula   C.sub.3 N.sub.5 (C.sub.6 H.sub.5)(CH.sub.2 OR).sub.4-y (CH.sub.2 NHCOOR').sub.y,       (iii) oligomers of (i) or of (ii), and   (iv) mixtures of at least two of any of (i), (ii) and (iii),     wherein the R and R' groups are, independently, radicals derived from monoalkyl ethers of alkylene glycols having at least 4 carbon atoms and monoaryl ethers of alkylene glycols having at least 8 carbon atoms, alone or combined with alkyl groups having from 1 to 20 carbon atoms, where x is in the range of from 2 to 6, and where y is in the range of from 2 to 4, or   wherein the R groups are, independently, hydrogen or alkyl groups of from 1 to 12 carbon atoms, where the R' groups are; independently, alkyl groups of from 1 to 20 carbon atoms, where x is in the range of from 2 to 6, and where y is in the range of from 2 to 4, or   wherein the R groups are, independently, hydrogen or alkyl groups of from 1 to 12 carbon atoms, where the R' groups are, independently, beta-hydroxyalkyl groups of from 2 to 18 carbon atoms, alone, or combined with alkyl groups of from 1 to 18 carbon atoms, where x is in the range of from 3 to 6, and where y is in the range of from 2 to 4.